Letters
by Echo-Dollhouse18
Summary: It started as an innocent request from his sister. Now it's all over school and he just can't say no. Read about Castiel's in-school business with his partner in crime, Dean Winchester.
1. Anna

This is a small idea I had...that grew a lot.

Disclaimer: I own no Supernatural people. Which makes me sad.

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><p>It started out as an innocent request from his sister.<p>

As most life changing and ridiculous things start from his siblings.

"Help me write a love letter!" Anna had practically yelled as she entered his room. Without knocking.

"What?"

"A love letter. To Balthazar. Write it for me. Please?" she begged. Actually getting on her knees right next to Cas as he sat in his desk chair attempting homework.

"Why not write it yourself? You are the one feeling the emotion. It would be simpler for you to do it." Cas explained turning back around to focus on his math.

"You're the good writer." Anna whined. "You write short stories all the time and you read. A lot."

"I've yet to be in love, Anna. I wouldn't know what to put." Cas attempts again.

"But the thing with Meg?"

"A crush. Nothing more."

It got silent. Cas was doing his math and waiting for whatever his sister was gonna bribe with to do this.

"10 bucks."

"No."

"15?"

"Anna-"

"20!"

"Would you-"

"25! Final offer."

"I'm not going to take your money." Cas sighed finally looking at his sister.

"Please, Cas? I'm desperate." Anna whispered looking up at him, still on the ground.

"Fine." Cas sighed.

He had to cover his ears from his squeals of delight. And thanks.

"Thank you! Thank you! Thank you!" She said jumping up and squeezing the air out of him.

"Give me a while." Cas said turning back to his work.

"Sure, sure. Take all the time you need." She replied.

Cas thought she'd leave the room and forget all about this the next morning.

Except, she was sitting on his bed. Watching him.

"Now?" Cas asked exasperated.

"Sooner it is, the less time I'll bother you about it being ready." Anna explained with a smile.

Cas sighed. He got quiet to think of a plan of attack.

He grabbed a near by, small notebook and opened it to the first empty page, and grabbed a pen.

He turned to his sister and looked right at her. "Tell me, in your own words, why you love him." Cas said.

"Huh?"

"This is a personal love letter." Cas explained expecting this reaction. "I can't just make up feelings and quirks that you find "adorable"." He did the airquotes with his hands. "I want to know why you like him the best. What makes him better than the others. What attracted you to him. You explain these thoughts and answers to me and I'll make them sound...eloquent." Cas said for lack of a better word.

"So, I explain why I like him, and what I like about him and you'll make it sound pretty?"

"Basically."

"Alright. " Anna said. Then she blushed. "It's a bit odd talking to you about this."

"Just...don't make it sound-"

"Final?"

"Yes. If you were bragging to Tessa or someone about him like I'm sure you do at lunch some days. I'll make it sound final." Cas said trying to help her out.

"Yeah! I can do that." Anna said, suddenly excited.

Cas was grateful for the quiet that enveloped the room as his sister was thinking of the situation.

Don't get him wrong. He loves Anna, just as he loves Gabriel. But he does like having a small break between Gabriel teasing him at school and Anna coming to him with the latest gossip about most of the people who aren't aware he exist. Which is usually for homework, but he does enjoy it greatly either way.

"Well," Anna started, "he knows the best place to get wine despite being underaged?"

"Anna."

"I'm trying." Anna said, leaning down on the bed sighing. She started talking to the ceiling as she continued. "His smile is beautiful. Just seeing it makes my whole day." Cas could tell she was smiling from her voice. "He pretends to be a man-slut. I've overheard him with his soccer buddies bragging about bedding a girl from another school. But later, he punched the crap out of Zach cause he was forcing himself on a girl at a party. Balthazar comforted her. Nothing sexual, just sweet and comforting."

Cas writes every word out of Anna's mouth, remembering Zach getting expelled, the news and stories were different each time he heard them though.

Anna sits up and continues talking. "Whenever I'm feeling down, he gives me one of those little white, round flowers that grow everywhere. And when we talk, we never seem to have a problem starting or even continuing a conversation. It's the ending we have problems with. And on my end, it's because I want to continue it and stay just a little longer with him. I sorta think, or I hope, it's the same with him." Anna continued.

She kept saying little things about him that she liked, while Cas listened and wrote them all down.

This went on for about a half an hour before Cas had to insist on a pause.

"Hand Cramp." Cas explained flexing his hand.

"Oh, right." Anna said as the dreamy look she had on slowly disappeared as she realized what was happening around her. Her face grew as red as her hair.

"That should be enough." Cas said and he started massaging his hand. "I'll start after I finish my homework."

"Homework!?" Anna yelled standing up

Cas rolled his eyes. "Let me guess. You came here straight after your club."

"Shit!" was his answer as Anna ran out of his room.

Cas was working his wrist thinking of how much his sister explained to him today. He had a small smile as he continued his homework.

A couple days later he had finished the letter. And he had handed it to Anna to see if it was what she wanted. So she was reading it. A loud.

"...Awaiting your answer, Anna Milton." She finished.

"Was that satis-Offph"

Cas was surprised by his sister's hug. She had practically leapt from her spot on the edge of his bed and onto him.

She pulled away with tears in her eyes. "This is beautiful, Castiel. Thank you."

"No problem Anna." Cas said patting his sister's back.

Gabe had walked in on the touching hug.

"Seriously? All deep moving, and emotional hugs have to have me We've been over this." Gabe said joining in on the now family hug.

It lasted a few more seconds until they all pulled back.

"Whats with the hug?" Gabe asked.

"He finished the letter!" Anna said excitedly.

"You guys were serious about that?" Gabe asked looking at them both.

"Yes." Cas replied.

"And its beautiful and lovely." Anna said smugly.

"Good. Now you just have to give it to him." Gabe said as they all headed downstairs to head to school.

Anna froze on the stairs.

"Give it to him." Anna repeated, clutching her bag strap so she didn't harm the letter.

"Yeah." Gabe said looking at her.

"Right." Anna said trailing off

"We're going to be late." Cas said looking at her.

"I don't think I can." Anna finally said.

"What?" Cas asked.

"What if he says no? What if he doesn't even know who I am?" Then she gasped loudly. "What if he likes other hes?"

"Then you apologize to him, hang out with him, and before you know it, you'll have a Will to your Grace." Gabe said grabbing one of her wrists and dragging her down the last few steps and out the door.

"But-but-but-"

"No buts." Cas said, stopping Gabe from dragging her out the door and looked at her. "You came to your younger brother for help and paid him the money that you were saving for the paint set you've had your heart set on. If he's worth all that, then you can at least give him the letter that explains all that to him."

Anna stared at him for a few seconds, then nodded. "You're right."

"Glad that's settled." Gabe said. "But we're late so let's get this show on the road!"

Later that day, Cas was at his locker when Anna found him. She hugged him and told him she had a date that weekend.

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><p>So, I have a couple of chapters wrote up. Just have to type. Please R&amp;R, yes?<p> 


	2. Gabriel

Hey. This is short...thought it was longer. But it's not, and I like it the way it is.

Disclaimer: Own nothing Supernatural related...except items. Which I love.

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><p>Cas rolled his eyes and looked at his project partner who was laying down on his bed.<p>

"Sorry. My family doesn't respect boundaries." Cas gave as an explanation.

"Hey, Cassie. I have a favor." Gabe said sitting on the edge of Cas's bed, ignoring the other person. The guy laying on Cas's bed hurriedly moved his feet. "And I have the cash."

"Cash?" Cas asked.

"Yeah. What you did with Anna. The letter thing?" Gabe asked. "I want one."

Cas sighed and turned to his brother. "That was just-"

"Amazing. Balthy is quoting it all the time and some of the things you wrote-"

"Rewrote." Cas clarified. "Anna told me how she felt, I just reworded it and put it on paper."

"Yeah. Whatever." Gabe said flapping his hand at Cas. He then reached into his pocket and pulled out a few papers. "I wrote how this chick makes me feel and.."

"It blows?" His partner chimed in.

Gabe turned around and saw him. "Who are you?"

"Dean Winchester. I'm Cas's project partner in bio." Dean explained reaching his hand out.

"Didn't ask for a life story, Dean-o." Gabe said, ignoring the hand. He turned back to Cas. "So, make it work and I'll pay you. Deal?"

"It was just to help Anna, Gabriel." Cas attempted to explain again.

"Great! Thanks Cassie!" Gabe shouted handing the papers and cash to Cas and left the room.

Cas sighed and put the items away.

"What was that about?" Dean asked moving to the edge of Cas's bed.

"I wrote a love letter to Balthazar from Anna a couple of weeks ago. And now it seems Gabriel wishes for me to do the same for him." Cas explained.

"And they pay you?" Dean asked astonished.

"Yes. $25 each."

"Nice."

"Not really." Cas said sighing.

"What? You don't want money?" Dean asked laughing a little, but Cas could sense a underlaying meaning. Just wasn't sure what it was.

"Everyone wants money, Dean. I just don't like taking it from family members." Cas said slowly, as if diffusing a bomb.

"Then why charge them?"

"Anna offered, then crammed the money in my hands after she read the first draft." Cas said. "And wouldn't take it back."

Dean just nodded.

"So this animal cell model we have to make?" Dean asked reopening his biology textbook.

"They discussed their project and their work in other classes.

After Dean left, Cas started reading what Gabriel wrote and started rewriting it.

Dean came over everyday after school so they could work together. He would also read what Cas had written already.

Dean even gave him some points.

"It's to...flowery." Dean said once.

"Flowery?" Cas asked, appalled at the word.

"Yeah. Last time was fine cause it was from a girl. This one's from a dude. And to Kali, of all people. Flowery isn't good."

"She doesn't like...flowery?"

"Have you ever heard her talk? Or just saw her around her friends?" Dean asked handing the papers back to Cas.

"To be honest, I'm not even sure Kali is her real name." Cas admitted. He at least knew Balthazar before hand. He's never even seen this Kali his brother is head over heels for.

"She's one of those girls that's like...hates the damsel in distress thing. She knows she's hot and can kick anyone's ass." Dean described. "She goes through guys like...they're just old rags."

Cas nodded. "So no romantic sentiments?"

"Not like this man."

Cas nodded again. "Thank you, Dean."

Dean was shocked. "No problem, Cas."

With Dean's insight, Cas finished the letter in a few more days. With Dean looking it over.

After he gave it to Gabriel, Gabriel immediately read it. Sat down and read it. In the middle of their hallway.

"Wow." Gabriel said putting the letter down from his face. "This is PERFECT!" He shouted, hugging Cas.

"Really?"

"Yes!" Gabe said excitedly. "I was a bit worried you'd make it girly. But its great, Cassie!" Gabe said. He let go of Cas and looked at him and spoke in a serious tone. "Seriously, dude. Thanks."

"It's no problem." Cas said. "I was actually going in that direction, but Dean pointed it out to me that she wouldn't like it." He admitted.

"Well. Hope it goes over just as well." Gabe said running out the door.

While Cas was in the cafeteria eating with Dean and his friend's, Gabe shouted his name clear across the cafeteria.

"CASSIE! SHE SAID YES!" Gabe had yelled with his hands around his mouth. Once he locked eyes with Cas, he threw up two thumbs up. Cas gave him a thumbs up as well. Gabe shouted a "YEAH!" before campus security was chasing him to calm him down.

"It worked?" Dean asked amazed looking at Cas.

"Guess so." Cas said watching his brother throw someones lunch on the security officer that was closest to him. He then turned to Dean. "It was because of your insight that it worked so well. Thank you Dean."

"Uh...yeah. No problem, Cas." Dean said smiling.

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><p>So, Dean's in the story now! Yay! Reviews are love in internet form.<p> 


	3. Balthazar

Yay! More on this story! Please enjoy.

Disclaimer: Don't own Supernatural. Sadly.

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><p>"That is not how it goes." Castiel said as he was picking up his books.<p>

"That's totally how it goes." Dean defended leaning against the lockers near Castiel. "See. It's like this-"

"Castiel." Balthazar said sliding up on the other side of the boy with a grin.

"Hello Balthazar." Castiel greeted. He closed his locker and was about to head with Dean to get Sam and they were all heading to the library to study, then he was going to buy them all dinner.

Balthazar had other plans though.

"I have a few questions for the young Milton here." Balthazar said with a wink, directed at Castiel. "So the little stalker boytoy can leave now."

"This 'boytoy' was here first, jackass." Dean retorted, straightening his back.

"Balthazar, what is it?" Castiel asked, ignoring the glares that either guy had for the other.

Balthazar looked at Castiel, then at Dean. Then he shrugged, choosing to ignore Dean.

"Anna admitted that you were the one who wrote that letter to me." Balthazar said with a smile.

"I just organized her descriptions of events and of you as well as used different vocabulary." Castiel explained with a small sigh. "It was still her thoughts on you." He said, assuming it was about Anna not really feeling that way or some small thought process Balthazar was confronting them for.

"And _only_ hers on you." Dean said, glaring at Balthazar.

Balthazar laughed softly. "That's adorable, for an ignorant monkey like you, Winchester."

"If you're here for a favor maybe you shouldn't be insulting my best friend." Castiel said moving to be in between Dean and Balthazar.

"Right." Balthazar said. He stood straighter and glared at Dean when he smirked.

"Well. How much would you charge to write something for me?" Balthazar asked in a serious tone.

They both stared a them for a while, then Castiel spoke with the coldest voice either of them have ever heard.

"Did you, my sister's boyfriend, really just approach me so I could write you a love letter to someone else?"

"What?"

"That's what I heard." Dean said, more pissed than before.

"Hold-"

"That's a terrible man. What would Anna think?" Castiel asked motioning his head towards Dean. Still glaring at Balthazar though.

"Why-"

"You want me to hit him? I will gladly." Dean said, smirking and cracking his knuckles. He had a cold look directed at Balthazar, that shook him to his core.

"Dean-"

"Violence is never the answer, Dean." Castiel responded.

"That's right-"

"But it'll make me feel better. Most likely you too, Cas."

"Not rea-"

"Anna's a skilled fighter who has brought men twice her size down barely breaking a sweat." Castiel explained with what one can only describe as an evil-looking smirk.

Balthazar paled at that information.

"Can I at least watch her kick his ass?" Dean asked.

"HOLD ON JUST A BLOODY SECOND HERE!" Balthazar shouted stepping between the two men.

He waited a few seconds of silence before he spoke again. "Thank you. Now, Castiel, I wasn't asking for a bloody love letter." He said looking at the Milton. "I'm ecstatic with your sister and I love her dearly. Even before the letter, but that did help my confidence in pursuing the relationship. What I came to you about was a résumé." He explained, slowly. Making sure Castiel was listening to the words. "I want to get a seasonal job to buy Anna a great Christmas present."

Castiel looked at Dean, then he turned to Balthazar, nodding.

"Sure. But I need to know certain abilities about you." Castiel explained, calmed down know that he knows it was a misunderstanding.

"And it'll be a fraction cheaper than letters." Dean supplied.

"That as well." Castiel agreed.

"It's settled then." Balthazar exclaimed happily. "Tomorrow after school. I'll let you know a few abilities I have. Leave the ape behind." He said motioning to Dean. Then he winked at Castiel and turned to leave.

"He's an ass." Dean said as they also turned to leave the opposite direction.

"I don't understand why the two of you don't get along." Castiel exasperated, following Dean out of the school and into his car.

"He just irks me." Dean explained, without really explaining. Castiel sighed and so Dean changed topics. "You gonna start offering to do people's resumes now?"

"He's doing it for Anna. I can't say no to that." Castiel explained.

"And the last three love letters you've done?" Dean asked, genuinely curious.

Dean and Castiel had started hanging out more and more after their project, and for every letter Castiel had, he went to Dean after he got the information on the people and the money to learn about the person he was writing to and writing for.

"They already had the money, Dean. And it's their words that they wish to convey to their loved ones. Just worded differently."

"Hey, man. I'm not judging you. Especially since you're paying me to help ya." Dean said. "Just want to know what to tell people. A love letter writer and a professional resume writer. Need to know what's happening."

"I'd rather not do this much more. But if they pay and are honest with their intentions, who I am to say 'no'?"

Dean sighed. Then clasped Castiel on his shoulder and smiled at him. "You're a good guy, Cas. But if there's too many customers, tell me. I can do damage control."

"Hopefully, it won't get to drastic." Castiel said with a small smile. "But thank you for your offer, Dean."

After that, they went to fulfill their plans.

Then, the next day, after school, Castiel and Balthazar spent about an hour perfecting his résumé. He made sure it sounded like Balthazar. He also had researched some test questions and answers that Castiel printed out for him.

Dean had come along and took jabs at Balthazar when he couldn't help it, but he also paid great attention to the information as well.

It ended up being successful and Balthazar got a job for the season that paid for all his presents.

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><p>Please Read and Review! Thanks!<p> 


	4. Lucifer

Hey! This is the new chapter! Love it! Sorry if that was really aggressive.

Disclaimer: Don't own Supernatural...sadly

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><p>A few weeks after winter break, Castiel hasn't had many customers, but he has spent more time with Dean.<p>

Well now he has a client.

He was in gym class. Him, along with a few other classmates were running around the track rather than join in the soccer game in the field.

"Castiel Milton." Lucifer called while running up to the boy.

"Yes, Lucifer?" Castiel asked once he was caught up.

"I heard you write stuff for money these days." Lucifer said smiling. "I want to hire you."

"No." Castiel replied, starting to walk away faster.

Lucifer jogged up to keep up with the younger. "Would you at least listen to what I want. One of each."

"Each?" Castiel asked, slowing down to look at him.

"A love letter and a résumé." Lucifer clarified.

"To who? And why?" Castiel asked. They started to slow down on the track to talk.

"Does that really matter?" Lucifer asked a bit defensively.

"The love letter's are written in a different way each time. They written in a way that's suppose to appeal to the recipient so they will consider you. Not accept, consider. If they accept it's up to them. And the resumes I agree to write must have a valid reason otherwise I will reject the offer." Castiel explained, repeating what he usually says to the people seeking his services.

"In that case, Meg Master's." Lucifer said, a bit hesitantly, but he knew he had to.

Castiel nods. "Alright. And the résumé?"

"I want to get a job before Mike." Lucifer said with a smug grin. "It'll irk him to no ends if I get one before him."

"I'll take the love letter only. And that's only if your completely serious." Castiel said, running a head again, deciding he was done with this conversation.

"Wait up!" Lucifer called out running to catch up to him. "I'll pay you more than your usual rate!"

That stopped Castiel's running and he resumed walking, waiting on Lucifer to join him.

"How much?"

"$100." Lucifer panted out, hands on his hips.

"That's almost triple." Castiel said, eyeing Lucifer. Looking for a tell, or something to prove Lucifer was just messing with him.

"I know." Lucifer said with a smile, finally caught his breath. "There's more to the job thing, but that's all I want to share. And I am completely serious about Meg." He said the last part looking at Castiel in his eyes.

Castiel contemplated this. $20 to $25 had been his rate for the love letters, depending on how long the letter was, and $10 for resumes. He couldn't accept all that money.

Except, Dean had been talking about how he wanted to get Sam _The Hobbit_ book series.

Plus Dean's birthday was soon.

Maybe, he could buy the books for Dean, so he could have them and share with Sam. Cause Castiel knew Dean loved that series as well.

"Deal. I'll need the money by tomorrow. Which is when we'll meet and do the résumé and start the letter." Castiel said, finalizing the deal.

Him and Lucifer shoke hands.

XxXx

"He's a bad guy Cas!" Dean yelled once he found out about their new client.

"Not that bad."

"He's violent as hell."

"Those are most likely rumors." Castiel said, defending their client, as they headed to the meet-up place.

"Every rumor has a grain of truth."

"You're thinking of lies, Dean."

"Nope. Pretty sure it's rumors, jokes, and lies."

"Just because you're not fond of him doesn't mean he's a terrible person and therefore can't be a customer." Castiel said, dead toned and rolling his eyes at Dean's behavior.

"That's exactly what it means Cas." Dean argued throwing his hands up.

"If I didn't take customer's because of your feelings we'd never have a male client base. Or women for that matter."

"What's that suppose to mean?" Dean asked, defensive.

"For every male client that comes to me, you assume it's for bad reason's and get angry with them. You assume they want it for terrible reasons, which is understandable." Castiel said, stopping Dean from arguing with him more.

"It's more than understandable, Cas. Some guys might be using these letter's for the wrong reason."

"That's why I always have you meet with them with me." Castiel said, matter-of-factly. Dean was stunned silent, waiting for Castiel to explain more so. "I can't read people well, unless I actually know them. You can read them very easily, and I relay on that skill you have. When the guy's are acting like they only want it for...wrong reasons. Then you act differently, and I can only read that because I consider you my closest friend. Then I know they are wrong for our business and I refuse them."

"Oh." Dean said, surprised at all that Castiel said.

"So we are meeting up with Lucifer, and doing his résumé. Then we are getting his information on the female he likes, and if he isn't sincere about her, you will be able to tell, as you always have been, and I will read that off of you, as I have been, then we will refuse the letter part of the agreement. Sound good?" Castiel asked Dean outside of the library.

Dean gave a small smile and nodded. "Yeah. Sounds good."

Castiel nodded and they headed inside the library.

They had spent two hours with Lucifer.

The first hour and a half was Lucifer reciting false skills that he thought he needed to actually getting a job. Cas figuring out that he was lieing by having Lucifer explain what the skill he said was and how he used it or where he learned it. Dean asking how the skills he knows Lucifer possesses can be worded well, which actually helped the process move faster.

And the last half hour was Lucifer reciting what he loves about his girl. Lucifer refusing to let Dean know the name of the girl, was proving difficult near the end.

"Just call Meg by her name damnit. This is ridiculous." Dean said when Lucifer was thinking about how to describe her, but not too much.

Both Castiel and Lucifer sighed in relief when Dean said this.

"When did you figure out it was her?" Castiel asked when him and Dean were leaving the school.

"Dude. It was either her or Lilith. And Meg's a brunette. That was like the first thing he said he loved about her. Think he has a hair fetish or something." Dean said, shivering at that thought.

Castiel had laughed at it instead.

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><p>...yeah. Had Luci like Meg. Meh. Please read and review! It's how I survive.<p> 


	5. Micheal

So...Hi. Please don't give up on me. The updates might be a little more spaced out, as they have been. Sorry.

Disclaimer: Don't own Supernatural. But listening to the musical soundtrack!

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><p>The day after Castiel and Dean had written Lucifer's resume, during lunch, Micheal sat in the seat that was open, next to Cas.<p>

"Castiel Milton." Micheal began, looking at the boy, and ignoring all the questioning stares from the rest of the table inhabitants. "I hear you have, well, I'd call it a business, but it sounds to shabby for it to actually be so. So I'll call it a company-in-progress."

"Micheal Novak." Castiel replied, not even looking up from the book he was reading this lunch period. "What do I owe this terribly inconvenient visit?"

There were a few whispers from the people around them, which was understandable. Micheal was a senior and never interacted with younger students. Not even the one's on his team.

Micheal sneered at the question, but he cleared his face by the time Castiel had put a bookmark in his book and looked up, setting the book aside for the moment.

"I just heard that you were so kind to take up Lucifer's offer, and I thought, since you were that kind to him. You would be that kind to me as well." Micheal said with a smile that didn't reach his eyes.

Castiel raised his eye brow, looking at the senior. "You obviously can't be talking about using my services, that you just insulted, to be a part of a sibling fight, are you?"

"Of course not, my dear Castiel." Micheal said, leaning forward, laughing slightly. "I just read a copy of Lucifer's resume and figured, if you could make...him," Micheal said 'him' like it was causing him pain to say so, "sound appealing, then you could probably make me sound incredible."

"And if I do that, I'd get caught in the petty sibling rivalry you guys have."

Micheal sighed at this. He dug into his pocket, producing a folded up printer paper with two $20's paperclip to the paper. He placed it on top of Castiel's book.

"A list of my skills and extra circular activities. If you do it, you stay neutral in our "petty sibling rivalry." You reject me, you've picked your side and you best be ready for that consequence." Micheal said getting up. "Consider the money a down payment. Another $20 for the finished product. Hope to see it soon."

Then Micheal turned his back to the table and walked away.

"What the hell was that about?" Dean asked, shocked at the events he saw occur just right across from him.

"The product of a terrible decision I made and an even worse sibling rivalry." Castiel said, putting the paper and money in his pocket.

"Then why did you agree to help Lucifer if you weren't ready for Micheal to call you out on it?" Dean asked, curious.

"I was...distracted." Castiel said, avoiding eye-contact.

"That's not like you Cas." Dean said smiling at his friend. Castiel looked at Dean, head tilted in confusion. "No offense, man. I just ment it's not like you to not think things through. Nice to know your human too." Dean ended with a smirk.

Castiel just nodded. "So what did you think of the first draft of Lucifer's letter?" He asked, changing topics.

The next day, Castiel gave Lucifer his love letter and Micheal his résumé. And vowed to never even bother them. Or accept another job from either.

Then he headed towards the book store, to buy Dean's present.

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><p>Short, I know. Next one's a bit short too. BUT the one after that...long.<p>

Please read and review!


	6. Dean

This is a short chapter, and the next one might take a while, but it will be up soon!

Disclaimer: Don't own Supernatural.

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><p>"Heya, Cas." Dean said, walking up the bleachers that hid behind a tree, and up to his friend. "Why're you out here?" He asked as he sat down, next to a Cas who was laying down in the shade.<p>

They were actually behind the school. It was quiet here, peaceful.

"The student body is annoying." Castiel stated with an annoyed tone.

Dean straightened at that. "Oh. Sor-"

"They should know, this close to summer break is for studying for finals. Getting certain affairs in order. The resume requests I've been getting, I understand. Not much, but I do. However, if they have me do all the work, how would they put together another one when they eventually leave that job?" Castiel asked no one. He was sitting up by this point.

"And I know," Castiel started again, "I know there are template's online. And English teacher's of the senior year give out example's of resume's. Gabriel told this to me. And he's a senior, so he should know, right?" He asked, looking at Dean.

Dean was looking at his friend. He had black circle's under his eyes. His whole body just displayed that he hasn't slept right in a few days. Maybe he just hasn't slept in a few days. That made Dean want to just have his friend over so he could hide all of Castiel's book and requests so he could just relax and sleep for a while.

"Yeah. He would." Dean said, agreeing to Castiel's statement.

"And then," Castiel began, "there's those people who hope a last minute confession will have them begin a wonderful love story romance. I was asked to write a few letters that scared me, Dean. They didn't describe love. They described the person;s schedule. Some have even wanted me to write death threats to their crush's other half. Or best friend of the recipient of their affection. One person wanted me to write a very detailed plan on maiming, dismembering, disemboweling, and destroying a body of her boyfriend's best friend. Who was another male."

"What!?" Dean asked, shocked at what Castiel was telling him right now.

He was present for some of the meeting's Castiel had described. The last one though, he was somewhere else.

"I didn't do it. Obviously. But I did take note of the name's of the people who have come up to me and were obviously in need of some deep help. I gave them to the guidance counselors." Castiel explained. Dean nodded at his friend's decision. "There were even some student's who wanted me to write fake acceptance letters to schools."

Castiel sighed and leaned back against the seat behind him. Dean felt powerless and he hated that.

"I believe I now know more about our senior class then I ever wished to know." Castiel said, trying to lighten the mood.

Dean laughed nervously. "Sounds like it."

Castiel turned his head to stare at his friend. They locked eyes for a while, until Castiel reached into his pocket and pulled out a couple of bills. More then a couple. Almost 10 bills.

"Your share for the last few letters." Castiel said handing them to Dean.

"Oh, yeah. Thanks man." Dean said taking them and pocketing them. He then looked up at the sky. "Want to come with me and Sam today after school? The last Hobbit movie is showing at the $3 movie theater. Then we were gonna get some dinner for the fam. Thinking KFC. Wanna join?"

Castiel smiled brightly at the thought. "Sound's great. I'd love to join you."

Dean nodded, glad he could help a little.

They stayed there the remainder of their lunch period, just relaxing in each other's presence.

Dean decided that he could write his own resume then.

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><p>Please Read and Review! It makes me smile!<p> 


	7. Cassie

Yay! Next Chapter!

Disclaimer: Don't own Supernatural. No matter how many times I dream and wish it to be.

* * *

><p>Castiel, Dean and Sam were at the library, doing their homework in one of the study rooms.<p>

Castiel left to get a book that would help him and Dean on an assignment

Dean had complained that it was too big of an assignment for being just a few weeks into the school year.

Castiel laughed softly just remembering Sam explaining to Dean the fundamental way of how school's work.

"Must be a good book." A girl said appearing next to Castiel.

Castiel looked at her. "Sorry. I was thinking of an earlier event. Am I in your way?"

"Oh. No." She replied. "I was actually looking for you I'm Cassie. Cassie Roberts."

"Nice to meet you Cassie. I'm-"

"Castiel Milton. Yeah. I know. Your pretty famous around school." She said, smiling shyly.

Castiel stood straighter and looked at the girl. He knew what this was about, all the girls that had approached him last year for a letter would act like how she is right now. Blushing and not looking him in the eye.

"Are you still doing them?" She asked, finally looking at him in the eyes. Determined.

So she's desperate, and determined.

"Yes." Castiel said, agreeing to another year of letters.

He really didn't mind. He enjoyed listening to people talk about who they loved. See their eyes light up. Their smiles. How their eyes focus out and they speak dreamily about the person.

He also enjoyed learning about the people who would come to him. He still is in contact with many couples he set up.

Cassie sighed in relief. "Good. Because I would like a letter. To, Dean Winchester." She said looking at him oddly.

Castiel was shocked still. "To whom?"

"Dean Winchester? If it's too odd, then we can just forget-"

"No." Castiel said hastily. He took a small breath and spoke again. "No. It's fine." He said, nodding to her. She smiled big. "We can meet up later to discuss this. Is that alright?"

"Of course! Tomorrow, after school, library. Good?"

Castiel thought about it for a moment. "The time is okay. However, the place isn't the best. How's outside, in the eating area?"

"Sure! Thanks, Castiel!" Cassie said walking away, with a big smile.

Castiel wasn't sure how he would go about this. He grabbed the books he came out of the room to get still in thought.

He usually went to Dean about the letters. Especially love letters. Dean knew the student body. They were only a few weeks into their new semester, their new year, and Dean already knew most of the freshmen year. He was amazing at making friends and around people.

Castiel entered the room, closing the door behind him.

He took his seat next to Dean and handed him the book.

"What took you so long?" Dean asked, looking at Castiel.

"I got approached for letter's." Castiel replied, easily. He wasn't sure how Dean would go about it. He didn''t seem to like them all that much.

"You doing those again this year?" Dean asked leaning on the table.

"Those love letter things?" Sam asked looking at Castiel.

"Yes, I enjoy it." Castiel explained, unsure of Dean's reaction.

"Cool." Sam said smiling.

"So, who's the person?" Dean asked, looking up at Castiel.

"Huh?"

"The client? Who are they? And when are we meeting them, cause I gotta say, it would beat the hell out of this." Dean grumbled shoving a notebook.

"It was a résumé." Castiel said, not looking at Dean.

"Ain't it a bit early to get a résumé? School just started." Dean asked looking at Castiel.

"Some people are over achievers." Castiel attempted to explain.

"Those kids should know how to write their own resumes." Dean grumbled and then grabbed a book. "Why do we need this book?"

Castiel sighed internally, thankful Dean bought those lies. He started explaining why he grabbed the books, and they returned to their homework.

XxXx

Castiel was nervous. He's never really meet a customer by himself. Dean was always there.

And he's there now.

"Dean?"

"Yeah?"

"Why are you following me?"

Castiel stopped moving to his destination, conveniently in front of the library. Dean had followed him since their last class. They were right across the hallway from each other.

"The résumé thing." Dean said slowly.

"Yes. But didn't you and Sam have plans today?"

"We rescheduled." Dean replied shrugging his shoulder's.

"You shouldn't have."

Dean was staring at Castiel, confused.

Dean always accompanied Castiel to every meeting. A résumé or love letter. Unless it was something He couldn't get out of, he would go.

"Should I...not have?" Dean asked, confusion in his voice.

"No! No. It's just... You and Sam have wanted to hang out by yourselves, yes? You can do it now. It's just a résumé, Dean. I can handle it." Castiel said, trying for a joking tone.

According to Dean's face, he wasn't buying it.

"If you say so." Dean said. He did leave Castiel, but they both knew that Dean didn't believe him.

Castiel watched Dean until he was sure he was out of sight, then he went past the library and to the outside eating area, where Cassie was waiting for him.

"Hey, Castiel!" She greeted.

"Hello." He said. He got out his pen and notebook, flipping to an empty page. "Did you already write down somethings, or are you-?"

"Oh!" Cassie said. She reached into her bag, looking for something. "I wrote down a few things, but not a lot."

"Alright." Castiel said, waiting patiently.

Cassie pulled out the paper, and gave it to Castiel. Who frowned.

"This is all external reasons." Castiel said, looking over the paper.

"Huh?"

"All the reasons you've written. They are all about his looks, basically."

"Is that bad?"

"Well, no." Castiel said looking at the paper. "How about you tell me a few things about Dean, not about his looks, that you like about him."

Cassie nodded, and started talking. Which impressed Castiel.

Usually the people who got the letter's acted like how Anna did when he did this. Nervous and taking a few times until they were comfortable around him enough. Dean usually helped in that prospect.

But Cassie just started listing things. That weren't that bad.

She was retelling the story of how she first met Dean. He saved her from some upper class girls who were being inflexible about her wanting to join the paper, even though she was only a freshmen. They were just being downright rude, and Castiel was going to talk to them, he had written two of the girl's letter's and another résumé. And Dean had stepped in, defended her, and started greeting her and talking to her now and then. That was last year.

She retold a few other stories, and just talked about Dean for a while.

When she was going into..certain territory, Castiel cleared his throat.

"I'm sorry." She apologized, blushing at what she was talking about.

"It's no problem. You're not the first person to go that far." Castiel explained. He looked at his notes. "This should be enough. Thank you."

"No. Thank you!" Cassie said happily. "I would do it myself, but I'm not good at writing romantic stuff. Better at articles."

"I understand." Castiel said nodding. "I should have a draft soon for you to look after if you wanted to."

"No, I'll just look at the last one." Cassie said.

She handed Castiel the money for her letter and said her good-byes and left.

XxXx

It was a week after that, and Castiel think's he got a good final draft written up.

"What's that?" Sam asked coming up from behind Castiel, scaring the writer.

"Nothing." He said, putting it away.

"Sure." Dean said, rolling his eyes.

Sam shrugged his shoulder's and looked at Castiel. "You coming to the library today?"

"Not today. Sorry." Castiel said, apologetically.

"Come on, Cas. With out you there, Dean's bothering me. And I'm not that good at getting him to focus." Sam begged.

"I will be done with this assignment today. Then I will come with you and help, tomorrow." Castiel said with a smile.

"I'm not that bad." Dean defended, crossing his arms over his chest.

"You only say that cause you don't have to deal with yourself." Sam retorted.

With that, the Winchester's left Castiel heading to the public library.

Castiel watched them until they got into Dean's car and drove off. Then he turned to the sitting area outside where Cassie was waiting for him.

"Hi Castiel!" She greeted happily as he sat across from her.

"Hello. I asked you here because I believe I have finished the letter." Castiel explained getting his binder out.

"Oh. Okay. Good. You have it? Good." Cassie said, nervously watching him.

"Yes." Castiel said, handing her a simple folder. "I am giving all the information you have provided me with back, the notes and the other draft. You can choose to use an older one or rewrite the letters. Most go with the final draft, but you can make your decision."

"Yeah. Thanks." Cassie said accepting the folder.

"I understand." Castiel said, looking right at her. She looked up at him and waited for him to continue. "Now that you have the letter, you have everything to tell him how you feel. Except the confidence that he feels the same way. I won't lie, some of my letter's haven't worked out." Castiel saw her tense up. "I also know that you truly have deep feelings for Dean. As you should. He is a great person." He had a small smile by this point. "He's the one that usually gives the people the confidence for the confrontation. He's better at that than me."

"He is a people person." Cassie said smiling as well.

Castiel took in a breath and continued. "I do hope this ends well for you."

He then got up and started to walk home, thinking over how he was going to start his homework.

XxXx

"Why did you do that?" Dean asked walking right up to Castiel.

Castiel was waiting on the curb of the parking lot. Dean told him he had a small thing to do after school and that he needed Castiel's help on their upcoming math test.

Castiel the book he was reading away and looked up at Dean, who was now standing over him.

"Do what?"

"The letter." Dean demanded holding up a couple of papers in his hands. "I know your handwriting, your wording, how you are about these things. Why?"

"She like's you and came to me for help. Much like our other clients."

"But you shouldn't have done this."

"Why? If you didn't like her then you should've just-"

"That's not the problem!" Dean yelled. He took a couple deep breaths to calm himself down. "The problem isn't about me liking her, it's the fact she came too you for a letter for me and you just agreed to it."

"How is that a problem?" Castiel asked deeply confused. He stood up to be on the same eye level with Dean.

"Because, she was using you to get to me. That just seems, dirty." Dean replied, shoving the letter into his backpack. "I know that seems selfish , or insane, but-"

"No." Castiel said, interrupting him. Dean looked into Castiel's eyes. "I get it. You don't want someone to use the people near you to get to you."

"Yeah."

"I understand." Castiel said with a small smile.

"Good."

They sat in silence for a while. Eventually sitting back on the curb.

"So," Castiel started, looking at Dean, "what did you say?"

Dean chuckled. He knew that Castiel was going to follow-up with his "clients", as he always did. Usually after a day or two, but he has been known to wait about one week at the longest.

"We have a date this weekend." Dean replied. "Have to give the girl a chance if she passes your test of true feelings."

Castiel nodded. "Good."

They waited a while longer, until Dean stood up and reached his hand out to help Castiel up.

"I desperately need help in math. These last couple assignments have been kicking my ass and we have a test on them tomorrow. Cram session?"

"You really shouldn't be cramming the night before, Dean. It's a bad habit." Castiel said, accepting the hand and standing up, face to face with Dean.

"Eh. I already have a few of them. What's so bad about adding another?" Dean asked with a smirk.

Castiel rolled his eyes in reply.

They both got in the car and headed off to Dean's house, where they were cramming for the test.

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><p>That is Cassie's story! And more detail about how Castiel does his work.<p>

Please read and review! Makes my day!


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